Beilstein J. Org. Chem.2024,20, 852–858, doi:10.3762/bjoc.20.77
boronmigration occurred during the hydroboration process of spiroviolene that resulted in the production of a mixture of 1α-hydroxyspiroviolane, 9α- and 9β-hydroxyspiroviolane after oxidation. The assertion of the cis-orientation of the 19- and 20-methyl groups provided further support for the revised
cyclization mechanism of spiroviolene.
Keywords: boronmigration; diterpene; spiroviolene; stereochemistry; Introduction
Terpenes represent one of the most fascinating families of natural products due to their structural complexity and diversity, as well as their indispensable biological functions that
the 9-organoborane intermediate IM-16 probably through borane–olefin complexes. The suprafacial nature of the boronmigration allowed the boron to be α-oriented in intermediate IM-16, which would give 10 with retention of the configuration after NaOH/H2O2 oxidation. The formation of a significant
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Graphical Abstract
Figure 1:
Structures of spiroviolene and related natural products.